- Enhanced catalytic activity of one-dimensional CdS @TiO2 core-shell nanocomposites for selective organic transformations under visible LED irradiation
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In this study, we are interested in the photocatalytic activity under visible LED irradiation of one- dimensional (1D) CdS @TiO2 core–shell nanocomposites (CSNs) prepared through a facile and convenient method. For the synthesis of 1D CdS@TiO2 core/shell structure, titania source (Tetrabutyl titanate) was hydrolyzed by water vapor transmission on the surface of CdS nanowires (NWs) which were prepared via solvothermal method. The characterization of 1D CdS@TiO2 core–shell nanocomposites (CdS@TiO2 CSNs) was performed using X-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), UV–Vis spectroscopy, and UV–Vis diffuse reflectance spectroscopy (DRS). The as-synthesized sample was utilized for the selective reduction of nitro compounds to benzimidazole and anilide, and also the reduction of benzophenones to alcohol under blue LED irradiation. The 1D CdS@TiO2 CSNs exhibited enhanced photoactivity compared with the pure TiO2, CdS nanowires and commercial TiO2-P25. The excellent reusability of the photocatalyst was examined for six runs. The results demonstrated that the prepared sample has the potential to provide a promising visible light-driven photocatalyst for other organic transformations.
- Eskandari, Parvin,Kazemi, Foad,Ramdar, Moosa,Zand, Zahra
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- Synthesis, structure-activity relationship and molecular docking studies of novel quinoline-chalcone hybrids as potential anticancer agents and tubulin inhibitors
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A new series of quinoline-chalcone hybrids was synthesized. The structures of these compounds were characterized by spectroscopic methods including 1H and 13CNMR and mass spectroscopy. The cytotoxic activity of compounds was evaluated against four human cancer cell lines including A2780 (human ovarian carcinoma) and A2780/RCIS (Cisplatin resistant human ovarian carcinoma), MCF-7 (human breast cancer cells), MCF-7/MX (Mitoxantrone resistant human breast cancer cells) and normal Huvec cells. The structure-activity relationship of synthesized compounds is discussed. Among quinolines 5e, 5g and 5j possessing benzoyl group showed significant cytotoxic activity against both resistant cancer cells and their parents. Compounds 5g and 5j, demonstrated the most antiproliferative activity with IC50 values ranging from 2.32 to 22.4 μM. They were also identified as tubulin inhibitors and induced cell cycle arrest at G2/M phase and apoptosis. Compound 5j induced more arrest at G2/M phase in four cancer cell lines compared to compound 5g. Finally, molecular dynamics simulation and molecular docking studies of compound 5j into the colchicine-binding site of tubulin demonstrated the possible interaction of this compound in the active site of tubulin.
- Mirzaei, Salimeh,Hadizadeh, Farzin,Eisvand, Farhad,Mosaffa, Fatemeh,Ghodsi, Razieh
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- Diversity Oriented Clicking (DOC): Divergent Synthesis of SuFExable Pharmacophores from 2-Substituted-Alkynyl-1-Sulfonyl Fluoride (SASF) Hubs
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Diversity Oriented Clicking (DOC) is a unified click-approach for the modular synthesis of lead-like structures through application of the wide family of click transformations. DOC evolved from the concept of achieving “diversity with ease”, by combining classic C?C π-bond click chemistry with recent developments in connective SuFEx-technologies. We showcase 2-Substituted-Alkynyl-1-Sulfonyl Fluorides (SASFs) as a new class of connective hub in concert with a diverse selection of click-cycloaddition processes. Through the selective DOC of SASFs with a range of dipoles and cyclic dienes, we report a diverse click-library of 173 unique functional molecules in minimal synthetic steps. The SuFExable library comprises 10 discrete heterocyclic core structures derived from 1,3- and 1,5-dipoles; while reaction with cyclic dienes yields several three-dimensional bicyclic Diels–Alder adducts. Growing the library to 278 discrete compounds through late-stage modification was made possible through SuFEx click derivatization of the pendant sulfonyl fluoride group in 96 well-plates—demonstrating the versatility of the DOC approach for the rapid synthesis of diverse functional structures. Screening for function against MRSA (USA300) revealed several lead hits with improved activity over methicillin.
- Barrow, Andrew S.,Cheng, Yunfei,Gialelis, Timothy L.,Giel, Marie-Claire,Kitamura, Seiya,Li, Gencheng,Moses, John E.,Ottonello, Alessandra,Sharpless, K. Barry,Smedley, Christopher J.,Wolan, Dennis W.
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supporting information
p. 12460 - 12469
(2020/06/10)
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- Iron-Enabled Utilization of Air as the Terminal Oxidant Leading to Aerobic Oxidative Deoximation by Organoselenium Catalysis
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In contrast to conventional organoselenium-catalyzed oxidation reactions that require peroxide oxidants such as hydrogen peroxide, in this work we found that, addition of a low loading of iron (II) could enable the successful utilization of air as the terminal oxidant in organoselenium-catalyzed oxidative deoximation reaction of ketoximes. This led to a new mild and relatively green aerobic oxidative deoximation method. Control reactions and X-ray photoelectron spectroscopy (XPS) analysis suggest that iron is crucial in the catalytic cycle, working to prohibit the deactivation of selenium catalyst through an iron-catalyzed aerobic oxidation of low valent selenium species by air to the active high valent selenium species. Since air can be utilized as the terminal oxidant, this work may contribute to the advance of organoselenium catalysis. (Figure presented.).
- Chen, Chao,Zhang, Xu,Cao, Hongen,Wang, Fang,Yu, Lei,Xu, Qing
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p. 603 - 610
(2018/12/14)
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- Palladium Catalyzed Direct Acylation of Iodo-Acetanilides/Iodo-Phenyl Acetates: Domino One-Pot Synthesis of 2-Quinolinones
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Pd-catalyzed direct acylation reaction of iodoacetanilides/iodophenyl acetates with aldehydes is presented. Simple, bench-top aldehydes were used as non-toxic acylating agents. This protocol comprises direct coupling with aldehydes without activating the carbonyl group and without directing group assistance. The strategy was applied to a domino one-pot synthesis of 2-quinolinones through acylation and intramolecular aldol condensation. Significantly, the strategy was extended to the domino one-pot synthesis of drugs and bioactive compounds.
- Basuli, Scuhand,Satyanarayana, Gedu
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p. 957 - 970
(2017/12/07)
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- Ketoprofen preparation method
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The invention provides a ketoprofen preparation method. The ketoprofen preparation method includes 1), taking phenacyl halide and acetanilide as raw materials, and subjecting the raw materials to Friedel-Crafts acylation to obtain 4-acetamido benzophenone; 2), subjecting the 4-acetamido benzophenone and 1, 2-dichloropropane to Friedel-Crafts acylation to obtain 2-(1-chloroisopropyl)-4-benzoyl acetanilide; 3), subjecting the 2-(1-chloroisopropyl)-4-benzoyl acetanilide to deprotection in an acidic condition to obtain 2-(1-chloroisopropyl)-4-benzoyl aniline; 4), subjecting the 2-(1-chloroisopropyl)-4-benzoyl aniline to alkali hydrolysis to obtain 2-(1-hydroxyisopropyl)-4-benzoyl aniline; 5), subjecting the 2-(1-hydroxyisopropyl)-4-benzoyl aniline to diazotization and reduction to compound 3-benzoyl-alpha-methyl phenylethanol; 6), oxidizing the 3-benzoyl-alpha-methyl phenylethanol to obtain ketoprofen. The ketoprofen preparation method has the advantages of non-existence of dangerous reaction process and high yield.
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Paragraph 0029-0031
(2017/07/01)
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- Preparation process of ketoprofen
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The invention discloses a preparation process of ketoprofen. A method takes benzoyl chloride and acetanilide as starting raw materials, and the ketoprofen is prepared through the steps of acylating, carting out acylation, de-protecting, hydrolyzing, carrying out diazotization reduction, carrying out Darzens reaction, oxidizing and the like. According to the method disclosed by the invention, the raw materials have cheap prices and are easy to obtain; the process is easy to realize and a hazardous process does not exist in the reaction; the yield is high and reaction conditions are moderate; the preparation method is simple and convenient to operate and has low requirements on equipment.
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Paragraph 0063; 0064
(2017/07/19)
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- Chemoselective generation of acyl phosphates, acylium ion equivalents, from carboxylic acids and an organophosphate ester in the presence of a Br?nsted acid
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We describe the chemoselective conversion of carboxylic acids to functional aromatic ketones promoted by a tailored organophosphate ester in the presence of a Br?nsted acid. The protonated phosphate ester reacts with the carboxylic acid to form acyl phosphate, which reacts with benzenes to give aromatic ketones, probably through the acylium ion or its equivalent. The reaction time is short even at room temperature, and the reaction is compatible with various other functional groups, including amines, olefins, esters, amides and nitriles.
- Sumita, Akinari,Otani, Yuko,Ohwada, Tomohiko
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supporting information
p. 1482 - 1485
(2017/02/05)
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- A versatile approach for the synthesis of para -substituted arenes via palladium-catalyzed C-H functionalization and protodecarboxylation of benzoic acids
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While a great number of ortho C-H functionalization reactions have been developed and several breakthroughs have been achieved in meta C-H activation, para C-H functionalization is still in its infancy stage. In this article, a versatile strategy for the synthesis of para-substituted arenes has been developed via a tandem process consisting of palladium-catalyzed C-H functionalization and subsequent copper-catalyzed protodecarboxylation of benzoic acids. Both electron-withdrawing and electron-donating functionalities can be introduced into the para positions of arenes bearing a variety of substituents.
- Pan, Shulei,Zhou, Bo,Zhang, Yanghui,Shao, Changdong,Shi, Guangfa
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supporting information
p. 277 - 281
(2016/01/20)
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- Photocatalytic synthesis of anilides from nitrobenzenes under visible light irradiation: 2 in 1 reaction
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An efficient method has been developed for the synthesis of a series of anilides via a two in one reaction of nitrobenzenes with anhydride in the presence of TiO2 as a nanocatalyst and photocatalyst under sunlight or blue LED irradiation. In this method simultaneously, nitrobenzenes convert to the corresponding anilines via photocatalytic reduction on the TiO2 surface, and a condensation of aniline with the anhydride performed on the Lewis acid site of the TiO2 surface. Interestingly amidation step leads to the promotion of better reaction and good selectivity in reduction of nitrocompounds. This method is simple, rapid, high yield, and green.
- Zand, Zahra,Kazemi, Foad,Partovi, Adel
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- An Efficient synthesis of Weinreb amides and ketones via palladium nanoparticles on ZIF-8 catalysed carbonylative coupling
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Heterogeneously catalysed carbonylative coupling reactions such as aminocarbonylation and Suzuki-carbonylation are reported using Pd nanoparticles supported on ZIF-8 for efficient and environmentally attractive synthesis of Weinreb amides and ketones from aryl bromides or iodides. The catalyst is air stable, offers high activity with very low palladium leaching and is recyclable. The presence of a phosphine ligand was required when aryl bromides were used as substrates, while no ligand was necessary when aryl iodides were used. the Partner Organisations 2014.
- Thanh Dang, Tuan,Chen, Anqi,Majeed Seayad, Abdul
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p. 30019 - 30027
(2014/08/05)
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- β-Cyclodextrin-TiO2: Green Nest for reduction of nitroaromatic compounds
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In this paper, highly efficient photocatalytic reduction of nitroaromatic compounds was investigated using β-cyclodextrin (β-CD) and commercial nano-TiO2 as a host-guest system in water under sunlight irradiation. The nitroaromatic compounds solubilized in water through encapsulation in β-CD formed an inclusion complex which was attached to TiO2 under sunlight irradiation. This 'guest-host system' that we call 'Green Nest' showed high efficiency for the reduction of nitro compounds to the corresponding amines, and more interestingly, one pot reductive N-formylation and N-acylation from nitroaromatic compounds can be carried out in the presence of triethyl orthoformate, acetic and benzoic anhydride. The β-CD-TiO2 was characterized by transmission electron microscopy, UV-visible spectra, thermogravimetric analysis, Brunauer-Emmett-Teller measurements, UV-visible diffuse reflectance spectroscopy, and Raman spectroscopy.
- Kakroudi, Mazaher Abdollahi,Kazemi, Foad,Kaboudin, Babak
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p. 52762 - 52769
(2015/01/16)
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- Synthesis, biological evaluation, and binding mode of novel 1-[2-(diarylmethoxy)ethyl]-2-methyl-5-nitroimidazoles targeted at the HIV-1 reverse transcriptase
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A novel series of 1-[2-(diarylmethoxy)ethyl]-2-methyl-5-nitroimidazole (DAMNI) analogues were synthesized and tested in cell-based assays and in enzyme assays against HIV-1 recombinant reverse transcriptase (RT). Preparation of the new derivatives was performed by reacting the appropriate benzhydrols or the correspondig bromides with 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole or the 3-hydroxypropyl homologue. Several compounds showed anti-HIV-1 activity in the submicromolar range. Structure-activity relationship studies suggested that meta substitution at one phenyl ring of the diarylmethane moiety strongly influences the antiviral activity. The 3,5-disubstitution at the same phenyl ring led to less potent derivatives. Molecular modeling and docking studies within the RT non-nucleoside binding site confirmed that DAMNIs, similar to other NNRTIs such as TNK-651 and delavirdine (BHAP U90152), assume a butterfly-like conformation that appears to be halfway between that of classical NNRTIs, such as nevirapine, HEPT, TBZ, TIBO, and DABOs, and the conformation of BHAPs. In particular, the diphenylmethane moiety mimics the wings whereas the 1-(2-methyl-5-nitroimidazolyl)ethane portion resembles the BHAP 5-methanesulfonamidoindole-2-carbonylpiperazine portion.
- Silvestri, Romano,Artico, Marino,De Martino, Gabriella,Ragno, Rino,Massa, Silvio,Loddo, Roberta,Murgioni, Chiara,Giulia Loi, Anna,La Colla, Paolo,Pani, Alessandra
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p. 1567 - 1576
(2007/10/03)
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- Palladium-catalyzed synthesis of aryl ketones from boronic acids and carboxylic acids activated in situ by pivalic anhydride
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A new palladium-catalyzed cross-coupling reaction between arylboronic acids and mixed anhydrides, generated in situ from carboxylic acids and pivalic anhydride, is presented. Optimization of the new catalyst and the reaction conditions led to the development of a convenient one-pot ketone synthesis directly from carboxylic and boronic acids in the presence of different (phosphane)palladium complexes in wet THF at 60 °C. Systematic studies were performed to elucidate the reaction mechanism of this transformation. The scope and the limitations of the new process are demonstrated by the synthesis of 33 functionalized ketones. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
- Goossen, Lukas J.,Ghosh, Keya
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p. 3254 - 3267
(2007/10/03)
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- Pd-catalyzed synthesis of functionalized arylketones from boronic acids and carboxylic acids activated in situ with dimethyl dicarbonate
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Highly efficient catalyst systems were developed that allow the palladium-catalyzed cross-coupling of arylboronic acids with carboxylic acids activated in situ with dimethyl dicarbonate at room temperature. As byproducts, only methanol, CO2, an
- Goo?en, Lukas J.,Winkel, Lars,D?hring, Arno,Ghosh, Keya,Paetzold, Jens
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p. 1237 - 1240
(2007/10/03)
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- A new practical ketone synthesis directly from carboxylic acids: First application of coupling reagents in palladium catalysis
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A new palladium-catalyzed cross-coupling reaction between arylboronic acids and carboxylic acids, activated in situ for the oxidative addition to a tricyclohexylphosphine palladium(0) catalyst by treatment with di(N-succinimidyl) carbonate (DSC) is disclosed, which allows the high-yielding synthesis of various functionalized arylketones under mild conditions.
- Goossen,Ghosh
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p. 2084 - 2085
(2007/10/03)
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- Stereoselectivity of methyl aryldiazoacetate cyclopropanations of 1,1-diarylethylene. Asymmetric synthesis of a cyclopropyl analogue of tamoxifen.
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[formula: see text] Dirhodium tetrakis(S-(N-dodecylbenzenesulfonyl)prolinate) (Rh2(S-DOSP)4)-catalyzed decomposition of methyl phenyldiazoacetate in the presence of 1,1-diarylethylenes results in intermolecular cyclopropanation with high enantioselectivity (up to 99% ee) and moderate diastereoselectivity (up to 80% de). The reaction was applied to the asymmetric synthesis of a cyclopropyl analogue of tamoxifen.
- Davies,Nagashima,Klino 3rd.
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p. 823 - 826
(2007/10/03)
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- Regiospecific acylations of aromatics and selective reductions of azobenzenes over hydrated zirconia
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Hydrated zirconia has been found to be an efficient and reusable catalyst for the regiospecific acylations of arenes and selective reductions of azobenzenes to produce benzophenones and hydrazabenzenes respectively.
- Patil,Jnaneshwara,Sabde,Dongare,Sudalai,Deshpande
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p. 2137 - 2140
(2007/10/03)
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- Method of using triaryl-ethylene derivatives in the treatment and prevention of osteoporosis
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The present invention relates to a method of using triaryl-ethylene derivatives in the treatment or prevention bone tissue loss or osteoporosis.
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- (Trichloromethyl)benzene: A versatile reagent for the preparation of substituted benzophenones
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Aromatic and heteroaromatic compounds were benzoylated efficiently with (trichloromethyl)benzene in 1,2-dichloroethane in the presence of aluminium chloride in good yield.
- Ayyanger,Lahoti,Srinivasan,Daniel
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p. 322 - 324
(2007/10/02)
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- Reinvestigation of a 5H-Dibenzotriazonine Synthesis
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Treatment of 5-chloro-2-aminobenzophenone (1) with o-phenylenediamine, sodium acetate, and acetic acid gave 2-(acetyl)amino-5-chlorobenzophenone (5) rather than N--1,2-benzenediamine (3), as reported by Kulkarni et al.Authentic 3 was prepared and treated with chloroacetic acid and polyphosphoric acid (PPA) to give 1, recovered 3, 2,8-dichloro-6,12-diphenyldibenzodiazocine (9) and 2-chloro-6-(chloromethyl)-13-phenyl-5H-dibenzotriazonine (10).Treatment of 5 with PPA, with or without chloroacetic acid, gave phenyl> phenylmethanone (11) as the sole product in 90percent yield.Treatment of other benzophenones, acetophenones, and anilines with sodium acetate and acetic acid provided acetanilides in 78-96percent yield, with the exception of 2'-aminoacetophenone (20), wich gave a quantitative yield of 2--4-methylquinoline (21).The mechanism of acetanilide formation with sodium acetate and acetic acid is discussed.The structure of 21 was established using high resolution 1H nmr techniques.Attempts to prepare an authentic sample of 21 from 2-chlorolepidine (26) and (20) gave 4-methyl-N--2-quinolinamine (29) as the major product.
- Peet, Norton P.,Sunder, Shyam,Barbuch, Robert J.,Whalon, Michael R.,Huber, Edward W.,Huffman, John C.
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p. 1611 - 1618
(2007/10/02)
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- SULL'ATTIVITA ANTIFUNGINA FITOIATRICA DI 4-AROILANILIDI
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Some N-acylderivatives of 4-aroylanilines were prepared and tested for phytoiatric antimycotic activity.The substances, most unknown, were subjected to in vitro and in vivo tests (in preventive phase).The compounds studied proved to have interesting activity.
- Massolini, G.,Carmellino, M. L.,Baruffini, A.
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p. 507 - 516
(2007/10/02)
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- Antiviral thiazolinyl benzimidazoles
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Certain thiazolinyl or thiazinyl ketobenzimidazole compounds and derivatives thereof are useful as antiviral agents.
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- Carbonyl-substituted 1-sulfonylbenzimidazoles
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Certain carbonyl-substituted-1-sulfonylbenzimidazole compounds are useful as antiviral agents.
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